Play It Smart
How managed service provider (MSP) and cybersecurity leaders build their businesses.
No vendors reading scripts. Operators opening their books: pricing changes that worked, niches they own, near-death moments, and the numbers behind all of it. Hosted by Alexej Pikovsky.
Latest episode
He Ran Security for The Weather Channel. Now He Keeps Factories and Fleets Online.
If a just-in-time supplier is late with a windshield, the entire plant shuts down, and John Penrod says the supplier can be fined $50,000 every 15 minutes. How his managed service provider (MSP) keeps customers like that running.
Season 2: inside the operator’s business.
Conversations on pricing, growth, artificial intelligence (AI) and the decisions behind an MSP. Listen below, with show notes and timestamped chapters for every episode.
He Ran Security for The Weather Channel. Now He Keeps Factories and Fleets Online.
Why This Healthcare MSP Moved Every Client to One Security Standard
He Sold His MSP to Private Equity. In 18 Months, Most Clients Left.
Six Private Equity Offers a Week, and He Sold to His Staff Instead
He Ran IT Inside the Agencies. Then He Started Serving Them.
The MSP Built for Clients Nobody Can Standardise
The $500K Wire That Turns an MSP Into the Defendant
Why a Three Person Fund Gets Billed for Ten Seats
Your Gross Margin Is Misreported and Misunderstood
Stop Selling to the Office Manager: How an MSP Owner Became the Board's vCISO
You Can't Take AI to Court: Why Compliance Still Needs Humans
Buying MSPs at 1-2x Profit While the Market Pays 5-8x
The Google-Only MSP That Turned Its Audit Into a SaaS
140 Clients, No Employees: How a Solo MSP Does It
The Fire Round.
Eight questions, the same every episode, answered fast. It's where the honest answers live. Compare how every guest calls cloud vs on-prem, or which client they should have fired sooner.
- One tool you couldn't run your MSP without?
- Most overrated thing in the MSP world right now?
- Most underrated?
- The client you should have fired sooner than you did?
- Best money you've spent on the business under $500?
- Cloud or on-prem in five years, in one word?
- One piece of advice for someone starting a solo MSP tomorrow?
- Finish this: the MSPs that survive the next five years will be the ones that...
Run an MSP with a story worth telling?
A niche you own. A pricing change that worked. A near-death moment you survived. Just the story of how you actually built it.
Pitch your story →
Your host, Alexej Pikovsky.
I work inside MSPs on sales and marketing systems, AI implementation and financial readiness for an exit. I’m the fractional chief revenue officer at Cortavo and the founder of NUOPTIMA. My background on the buying side of businesses shapes the questions I ask here: what makes a business grow, and what makes that growth valuable?
The rule of the show: guests bring numbers, the host brings questions.
Put the ideas to work in your MSP.
Know Your Number is a private room for MSP owners and a regular call with me on sales & marketing, AI and financial readiness.
Join the room →The research behind the questions.
Every episode stands on research. The full library lives on this site's Insights and on NUOPTIMA, the growth agency behind the show's production.